Synthese des DNA‐Gyrase‐Inhibitors Microcin B17, eines Peptidantibiotikums mit 43 Aminosäuren und acht aromatischen Heterocyclen im Peptidrückgrat

Videnov, Georgi; Kaiser, Dietmar; Brooks, Marc; Jung, Günther

doi:10.1002/ange.19961081316

Cited by 5 publications

(3 citation statements)

References 11 publications

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“…It is the latest in the series of impressive achievements in peptide synthesis, for example, the preparation of the membrane-pore-forming antibiotic alamethicin [10] and of the DNA-gyrase inhibitor microcin. [11] In the case of polytheonamide B (1), the stereoselective synthesis of nonproteinogenic amino acids in combination with solid-phase peptide synthesis and the coupling of peptide segments under mild conditions provided access to a complex peptidic structure of high biological relevance. The developed synthetic route also Figure 1.…”

mentioning

confidence: 99%

Convergence Leads to Success: Total Synthesis of the Complex Nonribosomal Peptide Polytheonamide B

Ducho

2010

Angew Chem Int Ed

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Beyond the ribosome: The highly cytotoxic 48 residue nonribosomal peptide polytheonamide B, proposed to act as an ion channel, was synthesized by the coupling of four building blocks. The assembly of these peptide segments required the synthesis of eight nonproteinogenic amino acids, including a unique sulfoxide. This first synthetic route towards polytheonamide B (see scheme) demonstrates the potential of state‐of‐the‐art peptide chemistry.

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confidence: 99%

Convergence Leads to Success: Total Synthesis of the Complex Nonribosomal Peptide Polytheonamide B

Ducho

2010

Angew Chem Int Ed

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“…B. der Synthese des Membranporen bildenden Antibiotikums Alamethicin [10] und des DNA-Gyrase-Inhibitors Microcin. [11] Im Falle von Polytheonamid B (1) …”

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“…Da die erhaltene Substanz spektroskopisch und chromatographisch mit natürlichem Polytheonamid B identisch war, konnte hiermit erstmals bewiesen werden, dass [10] und des DNA-Gyrase-Inhibitors Microcin. [11]…”

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Konvergenz führt zum Erfolg: Totalsynthese des komplexen nicht‐ribosomalen Peptids Polytheonamid B

Ducho

2010

Angewandte Chemie

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Jenseits des Ribosoms: Das stark cytotoxische 48‐mere nicht‐ribosomale Peptid Polytheonamid B, ein vermutlicher Ionenkanal‐Bildner, wurde durch Kupplung von vier Bausteinen synthetisiert. Die Herstellung dieser Peptid‐Segmente erforderte die Synthese acht nicht‐proteinogener Aminosäuren, darunter ein einzigartiges Sulfoxid. Diese erste Synthese von Polytheonamid B (siehe Schema) demonstriert das Potenzial moderner Peptidchemie.

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Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

Stankova

Videnov²,

Golovinsky

et al. 1999

J. Peptide Sci.

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Novel 5-ring heterocyclic building blocks are synthesized. These can be incorporated into analogs of peptide antibiotics such as microcin B17, which is a potent DNA-gyrase inhibitor that exhibits eight thiazole and oxazole moieties. In particular, the syntheses of imidazole and bisoxazole amino acids as novel peptidomimetics are reported, this includes a new procedure for the oxidative conversion of the intermediates oxazoline, imidazoline as well as oxazole-oxazoline into the corresponding heteroaromatic compounds. A mixture of 1,8-diazabicyclo-[5.4.0.]-undec-7-ene carbon tetrachloride/acetonitrile and pyridine proved to be a very effective and mild agent.

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Synthese des DNA‐Gyrase‐Inhibitors Microcin B17, eines Peptidantibiotikums mit 43 Aminosäuren und acht aromatischen Heterocyclen im Peptidrückgrat

Cited by 5 publications

References 11 publications

Convergence Leads to Success: Total Synthesis of the Complex Nonribosomal Peptide Polytheonamide B

Convergence Leads to Success: Total Synthesis of the Complex Nonribosomal Peptide Polytheonamide B

Konvergenz führt zum Erfolg: Totalsynthese des komplexen nicht‐ribosomalen Peptids Polytheonamid B

Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

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